The school-readiness of Hawai'i's children and the readiness of Hawai'i's schools for entering kindergarteners has been a topic of considerable thought and action in recent years. Indeed, Hawai'i's citizens have long made young children and their education a high priority. The first steps were taken as early as 1894 when the Samuel N. and Mary Castle Foundation was created to promote high quality early education and care for children ages 0-5. In the same year, the Kindergarten and Children's Aid Association Preschools of Hawai'i was established to offer teacher training and free kindergarten to Hawai'i's children. Much thought, research, and collaborative work across public and private agencies, early education and care programs, parents, K-12 education, and higher education systems have brought Hawai'i to this point. The Good Beginnings Alliance Master Plan, presented in 1996, and the School Readiness Task Force Report of 2003 have both spelled out incremental steps and moved Hawai'i closer to providing a coherent early childhood system for families and children. In this article, the author reflects on lessons that have been learned from work to date and points to some directions for the future.